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Thanks for the mention!
Matt
I have even set-up relay SMTP from to EC2 instances to a Slicehost slice that had the DNS and reverse DNS setup correctly and that worked like a charm.
Emails have been over-used for things that probably didn't need emails, I think that is changing!
The issue with giving users a whitelisted IP is that they may get blacklisted unintentionally by not handling bounces, spam reports, ISP rate limits, or unsubscribes correctly.
There are even further problems on specific sites such as social networks where users import their contacts to invite other users and these emails don't exist anymore or the ISPs have turned them into SPAM traps. SendGrid exists to solve these problems and we are currently working with cloud providers to give their users a “Planning to send mail? Sign up here.” option. We also allow and encourage our users to integrate with Return Path.
I am working in a company called MxM which aim to solve this kind of problem. We relay your emails through SMTP and rewrite the email for deliverability.
You don't pay if your email goes into spam because this is the problem we are solving.
We give away free emails to startups so they can try out our services.
We've used TriggerMail (http://sailthru.com/products/triggermail) by SailThru (Neil Capel's company) for a few client projects which does exactly this and offers a REST-based API for easy integration with our apps. Their deliverability rates are the highest we've seen.
Whenever developers can offload a problem like this to a third party API there is enormous value and a pretty compelling business model.